Book Holiday Homes in New Windsor

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Featured Holiday Homes in New Windsor

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Fishkill
The price is AU$531 per night from 27 Apr to 28 Apr
AU$531
includes taxes & fees
27 Apr - 28 Apr
When you stay at this vacation home in Fishkill, you'll be within a 10-minute drive of Northeast Regional Epilepsy Group and SplashDown Beach.
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

Warwick
With a stay at this vacation home in Warwick, you'll be within a 15-minute drive of LEGOLAND® New York and Lewis Woodlands.
Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick
Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska

Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska

New Paltz
A stay at this vacation home places you in the heart of New Paltz, a 5-minute drive from Mohonk Preserve Visitor Center and 6 minutes from Testimonial ...
Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska
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Spacious New Luxurious holiday house in lovely Hudson Valley

Spacious New Luxurious holiday house in lovely Hudson Valley

Poughkeepsie
The price is AU$1,461 per night from 1 May to 2 May
AU$1,461
includes taxes & fees
1 May - 2 May
With a stay at this vacation home in Poughkeepsie, you'll be within a 15-minute drive of Vassar College and Marist College.
Spacious New Luxurious holiday house in lovely Hudson Valley
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

Stony Point
Located in Stony Point, this vacation home is within a 15-minute drive of Bear Mountain State Park and United States Military Academy.
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

Hopewell Junction
Located in Hopewell Junction, this vacation home is in the mountains, within a 10-minute drive of Clarence Fahnestock State Park and Hudson Valley Research ...
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Catskills mountain gateway house.

Catskills mountain gateway house.

Bloomingburg
With a stay at this vacation home in Bloomingburg, you'll be within a 15-minute walk of Wurtsboro Ridge State Forest and Roosa Gap State Forest.
Catskills mountain gateway house.
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

Greenwood Lake
Located in Greenwood Lake, this vacation home is within a 5-minute drive of Greenwood Lake and Lion's Field Park.
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

New Windsor
With a stay at this vacation home in New Windsor, you'll be on a river, within a 10-minute drive of United States Military Academy and Hudson River.
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

New Windsor Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our New Windsor vacation homes are the perfect way for you to wing it.

Holiday houses in New Windsor let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of New Windsor in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local New Windsor adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in New Windsor with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of New Windsor vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

New Windsor Holiday Homes essential information

Accommodation
426 Holiday Homes
Lowest Price
AU$193
Highest Price
AU$1,461
Popular accommodation
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo, Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick, Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska, Spacious New Luxurious holiday house in lovely Hudson Valley, Updated Getaway w/ Pool & Hot Tub on < 3 Acres!, 1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views, Catskills mountain gateway house., BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view., Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

Top trending hotels in New Windsor

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2 out of 5
915 Union Ave, New Windsor, NY
Fully refundableReserve now, pay when you stay
The price is AU$193 per night from 27 Apr to 28 Apr
AU$193
includes taxes & fees
27 Apr - 28 Apr
Located in New Windsor, Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point is within a 5-minute drive of Hamilton Fish Bridge and National Purple Heart ...
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

3 out of 5
180 Breunig Rd, New Windsor, NY
Fully refundableReserve now, pay when you stay
The price is AU$240 per night from 27 Apr to 28 Apr
AU$240
includes taxes & fees
27 Apr - 28 Apr
With a stay at Homewood Suites Stewart Airport in New Windsor, you'll be within a 5-minute drive of National Purple Heart Hall of Honor and Hamilton Fish ...
Homewood Suites Stewart Airport
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY
Fully refundableReserve now, pay when you stay
The price is AU$207 per night from 22 Apr to 23 Apr
AU$207
includes taxes & fees
22 Apr - 23 Apr
When you stay at Overlook Lodge at Bear Mountain in Bear Mountain, you'll be in a state park, a 1-minute drive from Bear Mountain State Park and 7 minutes from ...
Overlook Lodge at Bear Mountain
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La Quinta Inn & Suites by Wyndham Middletown

La Quinta Inn & Suites by Wyndham Middletown

2.5 out of 5
551 Route 211 E, Middletown, NY
Fully refundableReserve now, pay when you stay
The price is AU$235 per night from 27 Apr to 28 Apr
AU$235
includes taxes & fees
27 Apr - 28 Apr
With a stay at La Quinta Inn & Suites by Wyndham Middletown-Goshen in Middletown, you'll be in a shopping district, within a 15-minute drive of LEGOLAND® New ...
La Quinta Inn & Suites by Wyndham Middletown
Don't see what you're looking for?
See all available properties in New Windsor
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.